VANDAL
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I think upgrading is never too late – the sooner creatures start growing in the city, the better. But that’s just my strategy – if you disagree, feel free to suggest alternatives; I’ll consider any advice.
P.S. Another point: you say to send troops to capture the second city, but you still have to find that second city, and along the way, you’ll encounter neutrals, and you won’t have enough troops left to capture the city.
That’s the point of early upgrades – then your troops won’t die (with wise leadership). So, you definitely need to upgrade one stack on day 1 (unless there are some special circumstances). And you can easily determine where the other city is located. Determine the general direction on the map and follow the road. Then you’ll come across neutrals guarding the passage – that’s the path to the neighboring city.
Here’s another question. If 2 or more cities are captured, is there any way to redirect creatures from the 1st city to the second so that you don’t have to move them across half the map in the 5th game?
Yes, it’s definitely cheating! I did the same thing, and it worked! But it’s probably just to take out the big guys at the beginning of the game. As for advice, you need to level up leadership, luck, logistics, and wisdom. In my opinion, these are the best skills in the game.